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Thanks for many valuable suggestions, NotBob!
My problems might be caused by a combination of the issues you mention:
- Tags, the small-scale testing I did seemed to get both tag data and artwork right straight out of iTunes (on a Mac), but perhaps the tag quality varies across the library?
- Hidden files, this seems right, when browsing folders in iDrive, folders with such ._ files have two versions, one proper and one ._. This seems to suggest that there are hidden files from the Mac
- HDD speed, this is a rather old WD drive so this could certainly be an issue. It handles a small-scale test well enough, but with 15,000 tracks it could be too slow. Do you know drives (above 150 GB) that seem to work well, even SSDs?
- The car has the "highest" iDrive (I think it's called Navi Professional)
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